Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | 4-Methoxybenzylamine | HCID 75452 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | tert-Butyl {3-[4-bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-7,9-dioxo-1,6,7,9-tetrahydro-8H-imidazo[4,5-h]isoquinolin-8-yl]propyl}[2-(3,4-dimethoxyphenyl)ethyl]carbamate | HCID 59645483 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178490315 | HCID 178490315 | 65% |
Reaction Steps
Pd2(dba)3 (5.6 mg, 5.12 μmol) and dppf (2.83 mg, 5.09 μmol) were added to a degassed (N2 for 30 min) mixture of tert-butyl {3-[4-bromo-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-7,9-dioxo-1,6,7,9-tetrahydro-8H-imidazo[4,5-h]isoquinolin-8-yl]propyl}[2-(3,4-dimethoxyphenyl)ethyl]carbamate (780 mg, 1.02 mmol), 4-methoxybenzylamine (533 μL, 4.08 mmol) and NaOt-Bu (196 mg, 2.04 mmol) in THF (10.2 mL). The reaction mixture was stirred at 60° C. for 3 h, then was concentrated under reduced pressure. The residue was purified by flash chromatography (40-63μ silica gel; CH2Cl2:acetone 95:5) to give the title compound (542 mg, 65% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07323567B2 |
|---|
| Source dataset | uspto-grants-2008_01 |
|---|
| ORD ID | ord-462a8938ecdc4dcaa09f155e689e2fe8 |
|---|
| Source note | uspto-grants-2008_01 |
|---|
